Having to overcome unexpected problems is a hallmark of entrepreneurship. Almost every business owner, artist, maker, and creative we know has had to deal with countless unexpected problems that arise in the journey and so we asked some brilliant folks from the community to share their stories of the unexpected problems they’ve faced along the way. 

Jibri Ross

One of the most pivotal challenges I faced on my entrepreneurial rise was the tornado we encountered last May. As I was preparing to expand my product line, that unexpected storm disrupted everything. In that moment, I was forced to pivot—something I hadn’t fully anticipated or planned for. Read More>>

Madison Schaefer

The biggest issue I have faced in my creative journey as a violist was actually physical. About four and a half years ago I had a very sudden and severe injury to my bow (right) arm while playing in orchestra. Read More>>

Mike Oppenheim

When I first started my career, it was in music. I played every instrument and had formed several bands growing up, so after college, I decided I would start a professional band, with my sights set on making it, which I defined as having a record deal and a touring act. Read More>>

Kelsea Martinez

The biggest problem and struggles I have faced in my journey have been my health constantly getting in the way. As an artist you need a lot of funds in order to really get somewhere in your music. Money for beats, to upload, to record, make videos, promote etc. In high school I began becoming ill. Read More>>

Michael Pitts

One of the most unexpected problems I’ve faced in my career happened early on when I was building my marketing consultancy, The Gentleman of Marketing. I had just landed some of my first real clients which were a chiropractor, lawyer, a nurse academy, a mortgage broker, and I was confident I could deliver results. Read More>>

Julian Qola

As an interpreter and translator (Portuguese/English) who worked in media, the rampant promotion and growing pervasiveness of artificial intelligence is an unexpected problem. Happening overtly, subtly, and with insufficient guardrails in either case, the skullduggery direction big-tech oligarchs have taken pegged inextricably to environmental and societal effects, as well as employment, is far more than I’m willing to discuss here. However, I will say this. Read More>>

Hilary Constable

The biggest unexpected problem occurred 2 months after my business launch party. I had just accepted several new writing projects from a long-term client. On my lunch break that day, I went for a bike ride and was hit by a pickup truck driver who ran a red light on a dedicated bikeway in my neighborhood. Read More>>

keith Lorren

From the very beginning, I was one of those entrepreneurs who believed in the magic of dreams, destiny, and reaching beyond what seemed possible. After graduating from business school, my family encouraged me to travel the world and pay attention to the signs the universe placed in front of me. Read More>>

Nei Marie

Some problems that I have faced that were unexpected were the lack of gigs and opportunity that Tennessee has for model ins in the entertainment industry and getting signed to an agency. Back in 2023 after I graduated Tennessee State University, I took a year off from my 9-5 to search for an agent that best suites me and that would sign me. Read More>>

Ernest Ayayo

One of the most unexpected problems in content creation is Life balance. Life is always unexpected and like a roller coaster. Medical problems like Heart failure and Diabetes have made it hard to pursue content creation. It put me in a long hiatus while I had to recover and even now it makes it hard to find unique things to do for the channel. Read More>>